Indium controlled regioselective 1,4-alkylarylation of 1,3-dienes with α-carbonyl alkyl bromides and N-heterocycles

被引:25
|
作者
Gu, Chang-Cheng [1 ]
Ouyang, Xuan-Hui [1 ]
Song, Ren-Jie [1 ]
Li, Jin-Heng [1 ,2 ,3 ]
机构
[1] Nanchang Hongkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China
[2] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
CONJUGATED DIENES; CATALYZED HYDROARYLATION; GAMMA-LACTONES; POLYMERIZATION; CYCLOADDITION; ALKENES; DIFUNCTIONALIZATION; 1,2-ALKYLARYLATION; FUNCTIONALIZATION; 1,6-ADDITION;
D O I
10.1039/c9cc08903a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We here describe a new, selective indium-promoted silver-mediated intermolecular oxidative 1,4-alkylarylation of 1,3-dienes with alpha-carbonyl alkyl bromides and N-heterocycles for producing functionalized N-heterocycles, which is characterized by its exquisitely controllable regio-/stereo-selectivity and excellent tolerance of functional groups. Mechanistically, the formation of the carbonyl-coordinated eta(3)-allyl-In complex radical intermediate is the key factor for successfully achieving regio- and stereo-selectivity toward 1,4-difunctionalization and (E)-isomers.
引用
收藏
页码:1279 / 1282
页数:4
相关论文
共 50 条
  • [1] Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
    Ye, Changqing
    Li, Yajun
    Zhu, Xiaotao
    Hu, Shengmin
    Yuan, Daqiang
    Bao, Hongli
    CHEMICAL SCIENCE, 2019, 10 (12) : 3632 - 3636
  • [2] Construction of Versatile N-Heterocycles from in situ Generated 1,2-Diaza-1,3-dienes
    Chen, Zhangpei
    Meng, Lingxin
    Ding, Zhiqiang
    Hu, Jianshe
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (02) : 164 - 187
  • [3] Synthesis of Benzofused N-Heterocycles via Rh(III)-Catalyzed Direct Benzannulation with 1,3-Dienes
    Zhou, Chu-Jun
    Gao, Hui
    Huang, Shi-Liang
    Zhang, Shang-Shi
    Wu, Jia-Qiang
    Li, Bai
    Jiang, Xianxing
    Wang, Honggen
    ACS CATALYSIS, 2019, 9 (01) : 556 - 564
  • [4] Regioselective and diastereoselective aminoarylation of 1,3-dienes
    Bao, Hongli
    Bayeh, Liela
    Tambar, Uttam K.
    CHEMICAL SCIENCE, 2014, 5 (12) : 4863 - 4867
  • [5] REACTION OF 1,3-DIENES WITH PHENYLMANGANESE CARBONYL
    GREEN, M
    HANCOCK, RI
    JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (01): : 109 - &
  • [6] Nickel-Catalyzed Dimerization and Alkylarylation of 1,3-Dienes with Alkyl Fluorides and Aryl Grignard Reagents
    Iwasaki, Takanori
    Min, Xin
    Fukuoka, Asuka
    Kuniyasu, Hitoshi
    Kambe, Nobuaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) : 5550 - 5554
  • [7] STEREOSELECTIVE AND REGIOSELECTIVE PALLADIUM-CATALYZED 1,4-DIACETOXYLATION OF 1,3-DIENES
    BACKVALL, JE
    BYSTROM, SE
    NORDBERG, RE
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (24): : 4619 - 4631
  • [8] Regioselective 1,4-Hydroamination of 1,3-Dienes by Photoredox/Cobalt Dual Catalysis
    Li, Pei-Ting
    Mou, Quansheng
    Yu, Wei
    ORGANIC LETTERS, 2025, 27 (08) : 1973 - 1978
  • [9] CHROMIUM CARBONYL PHOTOCATALYZED 1,4-HYDROSILATION OF 1,3-DIENES - SYNTHESIS OF ALLYLSILANES
    WRIGHTON, MS
    SCHROEDER, MA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (19) : 6235 - 6237
  • [10] Regioselective 1,4-addition of ammonia to 1-arylalka-1,3-dienes and 1-aryl-4-phenylbuta-1,3-dienes by photoinduced electron transfer
    Kojima, R
    Yamashita, T
    Tanabe, K
    Shiragami, T
    Yasuda, M
    Shima, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (03): : 217 - 222